It's hard to say for sure. Luffy has grown a lot in strength, but Rob Lucci is also a tough opponent. It could go either way depending on their strategies and determination.
In 'luffy vs kaido fanfiction', Luffy's growth and new abilities are often explored. He might develop new forms of his Gear powers to face Kaido. Kaido, being extremely powerful, forces Luffy to push his limits. Fanfictions may also focus on the intense battle scenes, with detailed descriptions of their attacks and counter - attacks.
Sure, there are numerous 'luffy vs naruto fanfiction' pieces. These fanfictions often explore not only the physical battle but also the clash of their personalities. Luffy's carefree and adventurous nature against Naruto's determined and often boisterous personality can make for some really engaging reads. They also might incorporate the different worlds they come from, the One Piece world and the Naruto world, to add more depth to the story.
I don't have the specific date for when the Egghead Arc started in manga off the top of my head. But you can probably find it by researching on manga-related blogs or by asking fellow manga enthusiasts.
The power comparisons are really interesting. Luffy's ability to stretch and his Gear forms against Naruto's Rasengan and other jutsu. It's like a clash of two very different power systems.
Another plot twist might be that Luffy actually loses the first round of the fight but then finds an inner strength or a new power - up from an unexpected source, like a memory of Roger or a new Devil Fruit ability that he unlocks in a moment of desperation.